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Here, two hydrogen\u2010bond interlocked planar molecules, HNAO and HPAO is reported, which coassemble with 1,2,4,5\u2010tetracyanobenzene (TCB) into charge\u2010transfer (CT) cocrystals NTC and PTC. The resulting NTC inherits two\u2010photon adsorption properties from HNAO, with the bathochromic shift enhanced by synergistic ESIPT and CT interactions, ultimately achieving near\u2010infrared emission. Remarkably, the intramolecular hydrogen bonds lock the molecule into a planar and ordered conformation, enabling regular face\u2010to\u2010face packing in NTC organic microwires and yielding the lowest optical\u2010loss coefficient (0.021\u00a0dB\/\u00b5m) of organic cocrystal to date, thereby demonstrating great potential for applications in optical computing systems. In contrast, the extremely low energy gap between the HOMO of HPAO and the LUMO of TCB in PTC drives a dramatically higher degree of CT in its excited states, predominantly facilitating non\u2010radiative transitions and resulting in non\u2010emissive behavior. Nevertheless, this trade\u2010off enables efficient NIR\u2010I photothermal conversion (\u03b7 = 47.7%) and excellent photostability, making PTC highly effective for rapid photothermal imaging and breakthrough time\u2010dependent information encryption applications. This work enriches the library of cocrystals and provides a novel strategy for tailoring the properties of cocrystal materials.<\/jats:p>","DOI":"10.1002\/advs.202515054","type":"journal-article","created":{"date-parts":[[2025,9,30]],"date-time":"2025-09-30T04:21:14Z","timestamp":1759206074000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Tunable Photoluminescent and Photothermal Properties of Organic Cocrystals Containing Hydrogen\u2010Bonded Interlocked Planar Molecules"],"prefix":"10.1002","volume":"12","author":[{"given":"Xinmeng","family":"Chen","sequence":"first","affiliation":[{"name":"Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction The Hong Kong University of Science and Technology  Clear Water Bay Kowloon Hong Kong 999077 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ling","family":"Zhu","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory of Green Chemistry and Chemical Processes Shanghai Frontiers Science Center of Molecule Intelligent Syntheses School of Chemistry and Molecular Engineering East China Normal University  Shanghai 200062 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shan","family":"He","sequence":"additional","affiliation":[{"name":"Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction The Hong Kong University of Science and Technology  Clear Water Bay Kowloon Hong Kong 999077 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bin","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Chemistry Sun Yat\u2010Sen University  Guangzhou 510006 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiang","family":"Lv","sequence":"additional","affiliation":[{"name":"Institute of Functional Nano &amp; Soft Material (FUNSOM) Jiangsu Key Laboratory for Carbon\u2010Based Functional Materials &amp; Devices Soochow University  Suzhou Jiangsu 215123 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xuedong","family":"Wang","sequence":"additional","affiliation":[{"name":"Institute of Functional Nano &amp; Soft Material (FUNSOM) Jiangsu Key Laboratory for Carbon\u2010Based Functional Materials &amp; Devices Soochow University  Suzhou Jiangsu 215123 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lin","family":"Xu","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory of Green Chemistry and Chemical Processes Shanghai Frontiers Science Center of Molecule Intelligent Syntheses School of Chemistry and Molecular Engineering East China Normal University  Shanghai 200062 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu","family":"Wang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Organic Integrated Circuit Ministry of Education &amp; Tianjin Key Laboratory of Molecular Optoelectronic Sciences Department of Chemistry School of Science Tianjin University  Tianjin 300072 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryan T. 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